Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (R)-3-(2-benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amine | HCID 24885301 | — |
| Reactant | Di-tert-butyl oct-7-en-1-ylimidodicarbonate | HCID 57933160 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Ammonia | HCID 222 | — |
| Product | di-tert-butyl[(7E)-8-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}oct-7-en-1-yl]imidodicarbonate | HCID 57933221 | — |
Reaction Steps
di-tert-butyl oct-7-en-1-ylimidodicarbonate (Preparation 48, 649 mg, 1.98 mmol), (3R)-3-[2-(benzyloxy)-5-bromophenyl]-N,N-diisopropyl-3-phenylpropan-1-amine (Prepared according to WO1994/11337, 560 mg, 1.16 mmol), palladium diacetate (27 mg, 0.12 mmol), tris(2-methylphenyl)phosphine (73 mg, 0.24 mmol) and N,N-diisopropylethylamine (0.304 ml, 1.75 mmol) were added to acetonitrile (6 ml) and the mixture was heated to 90° C. and left to stir overnight under nitrogen. Mixture was cooled and saturated aqueous sodium hydrogen carbonate and ethyl acetate were added. Organics separated and washed with saturated aqueous sodium hydrogen carbonate, brine, dried (magnesium sulphate) and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (100/0/0 to 96/4/0.4 by volume) to furnish the title compound as a oil, 530 mg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07612084B2 |
|---|
| Source dataset | uspto-grants-2009_11 |
|---|
| ORD ID | ord-6f12f1367def4b99b30b7f65ad290513 |
|---|
| Source note | uspto-grants-2009_11 |
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